6-Methylpyridine-2-boronic acid → (R)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-3-((S)-1-(4-(6-methylpyridin-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one

HRID 1046129Notes

Reaction equation

HRID 1046129 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@@:13]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)([CH2:16][CH2:17][CH2:18][OH:19])[O:12][C:11]2=[O:27])[CH3:9])=[CH:4][CH:3]=1.[CH3:28][C:29]1[N:34]=[C:33](B(O)O)[CH:32]=[CH:31][CH:30]=1>>[F:26][C:23]1[CH:24]=[CH:25][C:20]([C@:13]2([CH2:16][CH2:17][CH2:18][OH:19])[O:12][C:11](=[O:27])[N:10]([C@H:8]([C:5]3[CH:6]=[CH:7][C:2]([C:33]4[CH:32]=[CH:31][CH:30]=[C:29]([CH3:28])[N:34]=4)=[CH:3][CH:4]=3)[CH3:9])[CH2:15][CH2:14]2)=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 27627426-Methylpyridine-2-boronic acidHCID 59532370(R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-6-(3-hydroxy-propyl)-1,3-oxazinan-2-one

Product 1

HCID 58109134(R)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-3-((S)-1-(4-(6-methylpyridin-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one

Procedure

The title compound was prepared from (R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-1,3-oxazinan-2-one and 6-methylpyridine-2-boronic acid following a procedure analogous to that described in Example 1 Step 2. LC-MS Method 2 tR=0.868 min, m/z=449.2; 1H NMR (CD3OD) 1.28 (m, 1H), 1.56 (d, 3H), 1.61 (m, 1H), 1.95 (m, 2H), 2.23 (m, 1H), 2.34 (m, 1H), 2.46 (m, 1H), 2.55 (s, 3H), 3.11 (m, 1H), 3.46 (m, 2H), 5.50 (m, 1H), 7.06 (m, 4H), 7.19 (d, 1H), 7.31 (m, 2H), 7.51 (d, 1H), 7.73 (m, 3H).

Sources & evidence

ORD record
ord-a08583a5f50b47b981d0878ca5297e51
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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